反応 #83026

反応方程式

thionyl chloride

2-chlorophenylacetic acid

→

2-(2-chlorophenyl)acetyl chloride

反応条件

後処理

1. 1
   workup.DISTILLATIONThe reaction mixture was subjected to distillation
2. 2
   その他to remove the remaining thionyl chloride
3. 3
   その他to completely remove the thionyl chloride
4. 4
   workup.DISSOLUTIONThe residue was dissolved in 10 ml of dichloromethane
5. 5
   workup.ADDITION0.36 ml of triethylamine was added, with ice-
6. 6
   温度cooling, to a dichloromethane solution
7. 7
   workup.ADDITIONcontaining 0.40 g of 5-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzoazepine
8. 8
   workup.ADDITIONThereto was dropwise added the

実験手順

15 ml of thionyl chloride was added to 0.44 g of 2-chlorophenylacetic acid. The mixture was stirred at room temperature for 2 hours. The reaction mixture was subjected to distillation to remove the remaining thionyl chloride and then to azeotropy with toluene twice to completely remove the thionyl chloride. The residue was dissolved in 10 ml of dichloromethane. 0.36 ml of triethylamine was added, with ice-cooling, to a dichloromethane solution containing 0.40 g of 5-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzoazepine. Thereto was dropwise added the above obtained 2-(2-chlorophenyl)acetyl chloride solution. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was water-washed twice, then dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (elutant: chloroform/methanol=200/1) and then recrystallized from methanol-diethyl ether to obtain 0.29 g of 5-dimethylamino-1-{4-[2-(2-chlorophenyl)acetylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzoazepine.

出典